INTEGRATED METHODS FOR CHEMICAL SYNTHESIS

• US 20180030014A1
• Filed: 02/12/2016
• Published: 02/01/2018
• Est. Priority Date: 02/13/2015
• Status: Abandoned Application

• Current Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Original Assignee: Novomer, Inc (Danimer Scientific, Inc.)
• Inventors: SOOKRAJ, Sadesh H., SLOWIK, Michael A.
• Application Number:
  US15/550,300
• Publication Number:
  US 20180030014A1
• Time in Patent Office: Days
• CPC Class Codes: C01B 2203/062 Hydrocarbon production, e.g. Fischer-Tropsch process
• CPC Class Codes: C01B 2203/066 with fuel cells
• CPC Class Codes: C01B 2203/068 Ammonia synthesis
• CPC Class Codes: C01B 3/32 by reaction of gaseous or liquid organic compounds with gasifying agents, e.g. water, carbon dioxide, air
• CPC Class Codes: C01B 3/34 by reaction of hydrocarbons with gasifying agents
• CPC Class Codes: C01B 3/50 Separation of hydrogen or hydrogen containing gases from gaseous mixtures, e.g. purification C01B3/14 takes precedence
• CPC Class Codes: C07D 305/12 Beta-lactones
• CPC Class Codes: C07D 307/60 Two oxygen atoms, e.g. succinic anhydride
• CPC Class Codes: C10G 2/30 from carbon monoxide with hydrogen
• CPC Class Codes: C10J 2300/1656 Conversion of synthesis gas to chemicals
• CPC Class Codes: Y02E 50/30 Fuel from waste, e.g. synthetic alcohol or diesel
• CPC Class Codes: Y02P 20/10 Process efficiency

Abstract

The integrated processes herein provide improved carbon efficiency for processes based on coal or biomass gasification or steam methane reforming. Provided are also ethylene oxide carbonylation products such as beta-propiolactone and succinic anhydride having a bio-based content between 0% and 100%, and methods for producing and analyzing the same.

Claims

1. Beta-propiolactone produced by carbonylation of ethylene oxide having a pMC of zero, as defined by ASTM D6866, using carbon monoxide having a pMC greater than zero, as defined by ASTM D6866.

3. The beta-propiolactone of claim 1, wherein the carbon monoxide has a pMC of 107.5.

2. Beta-propiolactone produced by carbonylation of ethylene oxide having a pMC greater than zero, as defined by ASTM D6866, using carbon monoxide having a pMC of zero, as defined by ASTM D6866.

4. The beta-propiolactone of claim 2, wherein the ethylene oxide has a pMC of 107.5.

5. Beta-propiolactone produced by carbonylation of ethylene oxide using carbon monoxide, wherein one of the ethylene oxide and carbon monoxide has a biobased content greater than zero percent, and the other has a biobased content of less than 100 percent.

6. The beta-propiolactone of claim 5, wherein the ethylene oxide has a biobased content of 100%.

7. The beta-propiolactone of claim 5, wherein the carbon monoxide has a biobased content of 100%.

8. A method for producing beta-propiolactone having biobased content greater than zero percent and less than 100 percent, the method comprising carbonylating ethylene oxide using carbon monoxide, wherein one of the ethylene oxide and carbon monoxide has a biobased content greater than zero percent, and the other has a biobased content of less than 100 percent.

9. A method for determining whether a sample of beta-propiolactone was produced from a combination of bio-based and fossil carbon synthons, comprising:

(i) thermally decomposing the sample to ethylene and carbon dioxide;

(ii) determining the isotopic abundance of ¹⁴C in the carbon dioxide carbon; and

(iii) determining the isotopic abundance of ¹⁴C in the ethylene carbons;

wherein, if the isotopic abundances in (ii) and (iii) are not equal, the beta-propiolactone was produced from a combination of bio-based and fossil carbon synthons.

10. Succinic anhydride produced by carbonylation of ethylene oxide having a pMC of zero, as defined by ASTM D6866, using carbon monoxide having a pMC greater than zero, as defined by ASTM D6866.

12. The succinic anhydride of claim 10, wherein the carbon monoxide has a pMC of 107.5.

11. Succinic anhydride produced by carbonylation of ethylene oxide having a pMC greater than zero, as defined by ASTM D6866, using carbon monoxide having a pMC of zero, as defined by ASTM D6866.

13. The succinic anhydride of claim 11, wherein the ethylene oxide has a pMC of 107.5.

14. Succinic anhydride produced by carbonylation of ethylene oxide using carbon monoxide, wherein one of the ethylene oxide and carbon monoxide has a biobased content greater than zero percent, and the other has a biobased content of less than 100 percent.

15. The succinic anhydride of claim 14, wherein the ethylene oxide has a biobased content of 100%.

16. The succinic anhydride of claim 14, wherein the carbon monoxide has a biobased content of 100%.

17. A process for producing succinic anhydride having biobased content greater than zero percent and less than 100 percent comprising carbonylating ethylene oxide using carbon monoxide, wherein one of the ethylene oxide and carbon monoxide has a biobased content greater than zero percent, and the other has a biobased content of less than 100 percent.

18. A method for determining whether a sample of succinic anhydride was produced from a combination of bio-based and fossil carbon synthons, comprising:

(i) thermally decomposing the sample to γ

-ketopimelic acid and carbon dioxide;

(ii) determining the isotopic abundance of ¹⁴C in the carbon dioxide carbon; and

(iii) determining the isotopic abundance of ¹⁴C in the γ

-ketopimelic acid carbons;

wherein, if the isotopic abundances in (ii) and (iii) are not equal, the succinic anhydride was produced from a combination of bio-based and fossil carbon synthons.

19. A method for determining whether a sample of polyacrylic acid was produced from a combination of bio-based and fossil carbon synthons, comprising:

(i) thermally decomposing the sample in the presence of a copper catalyst at a temperature between 103°

C. and 216°

C. to carbon dioxide and a residue;

(ii) determining the isotopic abundance of ¹⁴C in the carbon dioxide carbon; and

(iii) determining the isotopic abundance of ¹⁴C in the residue;

wherein, if the isotopic abundances in (ii) and (iii) are not equal, the polyacrylic acid was produced from a combination of bio-based and fossil carbon synthons.

20. Beta propiolactone, wherein the beta propiolactone has three carbon atoms, and wherein two of the three carbon atoms in the beta propiolactone are bio-based and the third carbon atom is fossil-based.

21. The beta propiolactone of claim 20, wherein the carbonyl carbon of the beta propiolactone is fossil-based.

22. Beta propiolactone, wherein the beta propiolactone has three carbon atoms, and wherein one of the three carbon atoms in the beta propiolactone is bio-based and the other two carbons atom are fossil-based.

23. The beta propiolactone of claim 22, wherein the carbonyl carbon of the beta propiolactone is bio-based.

24. Succinic anhydride, wherein the succinic anhydride has four carbon atoms, and wherein two of the four carbon atoms of the succinic anhydride are bio-based and two of the carbon atoms are fossil-based.

25. The succinic anhydride of claim 24, wherein the two carbonyl carbon atoms of the succinic anhydride are bio-based.

26. The succinic anhydride of claim 24, wherein the two carbonyl carbon atoms of the succinic anhydride are fossil-based.